Founders share the biggest challenges of running a tech business

I asked over a dozen successful founders about the single obstacles they'd found most difficult to surmount on their business journeys.

Check out their answers below, and keep in mind these are all bootstrappers, so you won't find anything about raising money from investors here.

Waiting too long to spread the word

👤 Jay Caetano of AnarchoCoffee ($760/mo)

The biggest challenge for AnarchoCoffee has been spreading the message about the product. Other smaller obstacles include things like shipping and handling and just not having enough time or capital to grow the business. But I have to keep reminding myself that the company is only six months old as I am writing this. My only regret is not starting on the entrepreneurial path sooner.

Finding the right pricing model

👤 Sarah Hum of Canny ($50,000/mo)

Pricing is one of those things that never stops being a problem. You should constantly adjust as you learn and improve your product. A simple pricing change could have such a huge impact on your business. But it’s tough. On one hand, we have customers willing to pay hundreds of dollars. On the other hand, we have competitors coming in to undercut us at $10/mo. Product founders are notorious for charging too little.


👤 Martijn Wijtmans of Tripetto ($5,500/mo)

We’re still now learning how to most effectively sell Tripetto and to whom. That’s hard enough in itself and also takes time. In hindsight we should have found a way to work out the sales angle far more concretely and much earlier. In that regard self-funding has helped creativity and quality but also taken away a healthy dose of urgency.

Public relations

👤 Dmitry Dragilev of JustReachOut.io ($30,000/mo)

The biggest challenge has been learning about PR from a non-PR perspective. I approach PR differently than the leading agencies do because I am looking to scale my own business or the business of my customers differently than a massive multinational conglomerate would. The stories and products that spring from small companies need to be nimble and adjust their strategy quickly.

Insecurity about the product's quality

👤 Eelco Jellema of Sjabloon ($1,000/mo)

Early on I felt somewhat insecure about the product, and thus felt the need to list that more was “coming soon.” These promises made it a little bit stressful at times; when asked about certain features, I needed to explain how there was no set timeframe just yet. On the other hand, these “pre-announcements” gave me a better idea for the roadmap of Sjabloon, as some specific features were asked about more often than others.


👤 Mitch Colleran of Join It ($40,000/mo)

When building a business as a bootstrapped founder, there is a focus on the lack of capital, but one of the challenges that caught me off guard was how alone it feels. Without investors, there are fewer people to check-in with and hold us accountable. Without investors, you’re going to be slower to build the team, so it's just you for a much longer period of time.

Taking on a team-sized work burden as a solo founder

👤 Andrew Fedoniouk of Sciter Engine ($9,000/mo)

I am building, selling, and supporting an alternative to WebKit and V8 engines, which is no small task for one person. From the start, I was aware that I was taking on a huge project that other companies have devoted entire teams to, but I chose to look at it as more of a mental challenge than a technical one. I knew I had the skillset to pull it off, I just had to keep myself motivated and on track.

How long it takes to build a good product

👤 Hiram Nunez of Tee Tweets ($1,200/mo)

The number one thing I was blindsided by was the sheer amount of time it would take to actually build and run a business. You're probably thinking, "It's just a t-shirt company, how hard could it be?" I thought the same thing. Turns out: very. This is due to a number of reasons: supply chain logistics, product quality, content creation, manufacturing, and marketing.

Being a non-technical founder

👤 Taylor Jacobson of Focusmate ($700/mo)

Being a non-technical founder. This issue is such a meme but it's a serious problem. What should you do if you don't know how to code your own product? In the end, I built my first prototype myself using Wordpress, Zapier, Google Sheets, and ScheduleOnce. There are a ton of tools out there now to build prototypes without code. You can get started validating your product without learning to code, and this will help you attract resources and talent.

Delivering products to customers on time

👤 Dom Wells of Human Proof Designs ($90,000/mo)

We struggled a lot with operations when things really started to take off. We just didn't have enough people to meet the demand, and we ended up having to refund customers. Our reputation took a hit back then because those same people who now praise us in Facebook groups would go there to complain about how slow we were.

Serving customers in different timezones

👤 Gilles Bernhard of SCPlanner ($3,500/mo)

Timezones were a huge struggle at first, since all we do is based on planning events. It took a while to properly master this aspect of SCPlanner. We now have all the dates in UTC and the browser sets the timezone for the users.

Software marketing

👤 Ivan Mir of Qbserve ($2,000/mo)

The biggest challenge was a very naive understanding of how the modern internet economy works. The idea that good software is easy to promote is just as silly as the "good software sells itself" myth. I would definitely spend more time learning marketing. I still have a lot to learn, even after all the experience with Qbserve.

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  1. 3

    Having successfully failed to turn three businesses into a success (one in IT support, one in web development and one in WordPress plugins development) I can say that it's the lack of the business ability beyond your core strength that's the biggest challenge. Your product or service is only a small part of your business. Advertising, marketing, networking, administration, HR, managing growth, negotiating, accounting, customer support, chutzpah and more are all part of a successful business. Starting your own business requires a very broad skill set to succeed. If you want to be in business, the number one other skill you're going to have to learn is how to sell. And you will also require a certain amount of naivety.

    1. 3

      @theming, @nomis_mikah I think the idea of a co-founder is really significant. Steve and Steve at Apple, Bill and Steve at Microsoft, Larry and Sergey at Google, Scott and Mike at Atlassian etc. Even Facebook, which we all talk about Zuckerberg, is shown to have had five founders.

      If you can find someone to start your business with, they're going to not only bring different and complementary skills, but you'll each motivate the other on the other's tough days.

      Among failed businesses, it would be interesting to see the ratio of sole-founders to multi-founders. I bet it's comfortably skewed to the former.

      (My uncomfortableness and lack of confidence talking to people, selling my idea, is a part of why I attempted my businesses on my own. Which of course, that hurdle ultimately led to their not succeeding enough. The successes I did have were more circumstantial or accidental. 😁)

      1. 1

        @chrishowardau I'm working on projects solo, and yes, I do hope to have partners/teammates who could complement my weaknesses. I'm introverted, not good at selling.

      2. 1

        @chrishowardau It def. sounds like you need to partner up with someone. Why not make that your goal for 2020? Even if it's awkward force yourself to start reaching out and saying hi to people. For me it comes super naturally and for others it's super uncomfortable. I get that. But without that you'll sit there hoping someone will discover you. It doesn't hurt trying at least.

        1. 1

          @nomis_mikah Any tips for finding suitable cofounders/partners? Below are the general criteria of a suitable co-founder, in my opinion.

          1. Have the skills that we're lacking.
          2. Willing to take the risk of entrepreneurial path.
          3. Sharing same vision.
            I find it very hard to find all-match in my circle. Meeting #1 is not difficult, meeting #2 and #3 are the challenges for me. I'm trying to extend my circle, hope that's not too late.
          1. 1

            I would say firstly, how strong is your idea? Secondly, is it ambitious enough? I.e. if your were someone listening to it for the first time would you jump at the opportunity to be part of it? - google and watch Simon Sinek.

            I've created an idea for a business. Not an app. Not a landing page. Not a program. I have no beta. Nothing to show other than a pitch deck (which is essentially my thoughts down on paper). I'm running the idea past people to see if they're interested. I want to pre-seed it. Then once we get traction we'll make it happen. I'm not going to employ people who don't believe in what we're doing. I'm not going to sit convincing possible investors that they should be part of it. Anyhow, where do you sit and how are you selling your dream? Are you building an app, SaaS or something else... or as Jobs says are you trying to change the world?

    2. 3

      A solution to this could be finding right co-founders. This solution... is probably not as easy as it appears though.

      1. 2

        This is 💯 there's a lot of successful companies out there with two founders. Woz & Steve come to mind. Sometimes it's that relentless pushing from one founder that keeps things the momentum and the other that builds.

    3. 2

      I think this is really good (not the failures). You need different people to come together to start, build and grow something... and like everyone here on IH... it's really tough. I think if you're a creative brain then you should be matched with a business brain. What's worked incredibly well with Hunter is that my co-founder and I come at things from completely different angles. I develop the strategy, run the business and do the hustle, and he makes the work shine. Rallies the troops and brings the magic, Having said that we've all had huge ups and downs as entrepreneurs.

  2. 3

    Thanks for the list.
    The list is good but, unfortunately, it misses the main obstacle - the businessman himself/herself. It's the typical "survivorship bias" when the focus is on the people who survived and actually can't tell about obstacles that could prevent them from the success, therefore, they should be out of the interest.

      1. 1

        There is an interesting project, called Failory which may be very helpful (I really found it so :) https://www.failory.com/

        1. 1

          That's a pretty cool site. Thanks for sharing.

          1. 1

            No problem, thanks :)

        2. 1

          Thanks for this, looks interesting. Subscribed :)

  3. 2

    Very cool post! I'm interested in hearing more about virtual assistants. Has anyone else had success and what types of roles and tasks did you assign? This is completely new to me, so thanks in advance to anyone willing to share!

    1. 1

      I have an A.I. assistant called evie.ai. She schedules all my meetings for me. Sometimes with some many people to reach out to and different time zones it's been super helpful. Particularly late at night when I'm sitting on the couch. I can fire off an email and she'll make it happen. In relation to virtual assistant, I'd love to try someone who can project manage / service delivery. That's always one of the challenges in our business is keeping projects on track.

      1. 1

        Thanks for the reply and heads up about evie.ai! I’ll take a look more in depth this week. Seems like this could also help at my day job!

  4. 1

    These are helpful insights. Thanks for sharing! I look forward to seeing future round tables.

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